Depsipeptide

A depsipeptide is a peptide in which one or more of the amide (-CONHR-) bonds are replaced by ester (COOR) bonds.^[1]

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Depsipeptides have often been used in research to probe the importance of hydrogen bond networks in protein folding kinetics and thermodynamics. They are also found in nature as natural products. An infamous example is the L-Lys-D-Ala-D-Lac motif found in vancomycin resistant bacteria's cell wall building blocks. The amide to ester mutation disrupts its hydrogen bonding network with vancomycin, which is key to the antibiotic's activity.

Depsipeptide is an HDAC inhibitor being used in the treatment of some cancers where it is thought to reactivate silenced genes. It was first observed to have a positive role on gene expression in 1990. A clinical trial was conducted in 1996 for T cell lymphoma. [1]

References

1. ^ International Union of Pure and Applied Chemistry (1995). "depsipeptides". Compendium of Chemical Terminology Internet edition.